Abstract
Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.
Original language | English (US) |
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Pages (from-to) | 1138-1147 |
Number of pages | 10 |
Journal | Chemistry of Heterocyclic Compounds |
Volume | 43 |
Issue number | 9 |
DOIs | |
State | Published - Sep 2007 |
Externally published | Yes |
Keywords
- 1,1-dihydropolyfluoroalkyl sulfone
- N-chlorotriazole
- V-triazole
- X-ay structural analysis
ASJC Scopus subject areas
- Organic Chemistry